Tag: M.W=200-300

Reference of 24241-18-7, The chemical industry reduces the impact on the environment during synthesis 24241-18-7, name is 2-Amino-3,5-dibromopyrazine, I believe this compound will play a more active role in future production and life.

(a) Add 2-amino-3,5-dibromopyrazine (10 g, 39.54 mmol, 1 eq) to a 100 mL autoclaveAnd ammonia (50 mL, commercially available),Raise the temperature to 130 C under nitrogen protection conditions and carry out the reaction overnight (10 to 12 hours);Cooling, suction filtration,The obtained solid was vacuum dried to give 5.0 g of Compound II.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Amino-3,5-dibromopyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Suzhou Derivative Biological Technology Co., Ltd.; Liu Ke; (6 pag.)CN108395436; (2018); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, molecular formula is C6H8ClF3N4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride

The title compound was prepared using the method described in WO 2008/040974.A mixture of 3-nitropropionic acid (20.0 g, 0.168 mol), 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1 ,2,4]triazolo[4,3- a]pyrazine hydrochloride (48.0 g, 0.21 mol) in acetonitrile (400 mL) is cooled to 0 C and 4-methylmorpholine (16.9 g, 0.168 mol) is added, followed by N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC) (48.4 g, 0.25 mol) after 5 min. The resulting mixture is stirred at room temperature for 20 hours. The resulting mixture is concentrated to about 2/3 of its volume and ethyl acetate is added (750 mL). The resulting mixture is washed twice with water (200 + 100 mL), sat. aq. sodium hydrogencarbonate (200 mL), brine (200 mL) and dried with sodium sulfate. The resulting clear solution is concentrated under reduced volume and MTBE is added (100 mL). The precipitated white solid is filtered off, washed with MTBE (200 mL) and dried under reduced pressure to yield 38.8 g (79 % yield) of NTPT as white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 762240-92-6, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; STERK, Damjan; USTAR, Matjaz; ZLICAR, Marko; WO2011/151443; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-01-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

The synthetic route of Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Buckley, Benjamin J.; Majed, Hiwa; Aboelela, Ashraf; Minaei, Elahe; Jiang, Longguang; Fildes, Karen; Cheung, Chen-Yi; Johnson, Darren; Bachovchin, Daniel; Cook, Gregory M.; Huang, Mingdong; Ranson, Marie; Kelso, Michael J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 24; (2019);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, This compound has unique chemical properties. The synthetic route is as follows., category: Pyrazines

A solution of the compound 5a (2.20g, 8.00mmol), 3-bromo-5-chloropyrazin-2-amine (1.54g, 7.27mmol), potassium acetate (2.00g, 14.54mmol), Pd (dppf) Cl2 (0.15g, 0.20mmol), H2O (2mL) in dioxane (40mL) was heated to 75 C under N2 for 4 hours. Hexane (50mL) was added, the precipitate was filtered to afford the compound 5b as a brown solid (0.79g, 36%). MS: 277 (M+H) +.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 76537-18-3.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; MA, Cunbo; GAO, Panliang; CHU, Jie; WU, Xinping; WEN, Chunwei; KANG, Di; BAI, Jinlong; PEI, Xiaoyan; (82 pag.)WO2017/211303; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 1458-18-0, A common heterocyclic compound, 1458-18-0, name is Methyl 3-amino-5,6-dichloropyrazine-2-carboxylate, molecular formula is C6H5Cl2N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The mixture of methyl 3-amino-5, 6-dichloropyrazine-2-carboxylate (0.5 g, 2.26 nMol) , (1-methyl-1H-pyrazol-4-yl) boronic acid (0.43 g, 3.39 nMol) in dioxane (20 mL) was added Na 2CO 3 (0.57 g, 4.53 nMol) and Pd (dppf) Cl 2 (0.83 g, 1.13 nMol) at 100 . Then the mixture was stirred at this temperature for 2h. LCMS showed the reaction was completed and purified with silica gel chromatography to give a desired product methyl 3-amino-6-chloro-5- (1-methyl-1H-pyrazol-4-yl) pyrazine-2-carboxylate. LCMS: m/z (ESI) , [M+H] + = 268.6.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 1458-01-1, These common heterocyclic compound, 1458-01-1, name is Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A stirred suspension of S^-diamino-?-chloro-pyrazine^-carboxylic acid methyl ester (1 10 g, 542.9 mmol) in MeOH (500 ml.) at 5-100C (ice-bath) is treated dropwise with a suspension of lithium hydroxide (46.6 g, 11 11 mmol) in water (500 ml_). The reaction mixture is heated to 500C for 5 hours then cooled to room temperature and stirred overnight. The resulting precipitate is collected by filtration and dried in a vacuum oven to afford the title compound as the lithium salt (di-hydrate). [M-Li]” 187

The synthetic route of 1458-01-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; WO2008/135557; (2008); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

These common heterocyclic compound, 87486-34-8, name is 3,5-Dibromo-1-methylpyrazin-2(1H)-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 87486-34-8

Example 307c 5-Bromo-3-(1,3-dimethyl-1H-indazol-5-ylamino-1-methylpyrazin-2(1H)-one 307c To a solution of 307b (280 mg, 1.74 mmol) in i-propanol (7 mL) was added triethylamine (352 mg, 3.48 mmol) and 3,5-dibromo-1-methylpyrazin-2(1H)-one (H-005) (700 mg, 2.61 mmol). After being stirred at reflux for 6 h, the mixture was cooled to room temperature. The precipitate was filtered, washed with i-propanol (2 X 2 mL), and dried at 60°C under reduced pressure to afford 307c as a brown solid (560 mg, 92percent). MS-ESI: [M+H]+ 347.8.

The synthetic route of 3,5-Dibromo-1-methylpyrazin-2(1H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F.Hoffmann-La Roche AG; CRAWFORD, James John; ORTWINE, Daniel Fred; WEI, BinQing; YOUNG, Wendy B.; EP2773638; (2015); B1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 32111-21-0 as follows. HPLC of Formula: C4H3IN2

Example 42; Synthesis of Compound 76; Compound a from the synthesis of compound 74 (255 mg) was placed in an oven dried microwave reaction vial with CuI (53.3 mg) and K3PO4 (233.4 mg) and purged with N2. To this mixture was added iodopyrazine b and the vial purged again with N2 followed by addition of 1,2-cyclohexanediamine (62.8 mg) in 2.6 ml dioxane and N2 was bubbled into the solution for 10 min and the vial crimped. The reaction vial was placed in the microwave for 30 min. at 140 C. The reaction went to half completion and was worked up by filtering off the non-product solids, concentrating under vacuum, and purifying by flash to give 139 mg compound c (47% yield). Compound c was dissolved in 3 ml 1.0 M TBAF in THF and heated to 60 C. overnight. The reaction was completed by LCMS and was diluted with H2O, extracted with EtOAc, washed with brine, dried over MgSO4, concentrated under vacuum and purified by SFC to give the final compound 76.

According to the analysis of related databases, 32111-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rawson, Thomas E.; Safina, Brian; Dotson, Jennafer; Zhou, Aihe; Aliagas-Martin, Ignacio; Halladay, Jason; Liang, Jun; Rueth, Matthias; Zhu, Bing-Yan; US2007/37791; (2007); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 6966-01-4,Some common heterocyclic compound, 6966-01-4, name is Methyl 3-amino-6-bromopyrazine-2-carboxylate, molecular formula is C6H6BrN3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

. Step 2: 3-Amino-6-bromopyrazine-2-carboxylic acid[00140] A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (5.1 1 g, 22.02 mmol) and lithium hydroxide (2.637 g, 110.1 mmol) in MeOH (20 mL) and Iota¾0 (20 mL) was heated to 90 C for 2 hours. The reaction mixture was allowed to cool and neutralized with HCl and the resultant precipitate collected by filtration. The sub-title product was taken on to the next step without further purification (4.80g, 99% Yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-6-bromopyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DURRANT, Steven, John; KNEGTEL, Ronald, Marcellus, Alphonsus; O’DONNELL, Michael; REAPER, Philip, Michael; WO2011/143419; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 762240-92-6, These common heterocyclic compound, 762240-92-6, name is 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To the stirred reaction mixture of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyrazine hydrochloride(11) (300 mg, 1.32 mmol), TEA (0.55 mL, 3.95 mmol)and toluene (10 mL), substituted cyanates 12(a-e)/isocyanates12(f-j) (1.32 mmol) were added at ambient temperature.The reaction mass was agitated at 75-80 C until thecompletion of the reaction that was monitored by TLC. Thereaction mass was allowed to cool at ambient temperatureand it was washed sequentially with 3% aqueous HCl(5.0 mL) and then water (5.0 mL). The organic fraction wasconcentrated under vacuum at 50-55 C to obtain crudeproduct. It was purified by column chromatography using10-50% of EtOAc:hexane mixture as a mobile phase. N-(4-Fluorophenyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[1, 2, 4]triazolo [4,3-a]pyrazine-7-carboxamide (13a); White crystalline solid; m.r.: 206-208 C. IR (KBr, nu/cm-1):3360 (N-H, str); 1674 (C=O, str); 1544 (C=N, str); 1163(-CF3, str). 1H NMR (400 MHz; DMSO-d6), d, ppm (J, Hz):3.95-3.98 (2H, t, J5.2, Piperazine), 4.22-4.24 (2H, t,J5.2, Piperazine), 4.95 (2H, s, Piperazine), 7.08-7.13 (2H,m, Ar-H), 7.43-7.79 (2H, m, Ar-H), 8.9 (1H, s, NH). 13CNMR (100 MHz; DMSO-d6), d, ppm (J, Hz): 39.98 (-CH2-CH2-); 40.87 (-CH2-CH2-); 43.30 (CH2-C-), 114.79 (d,J22.0, CF3), 117.12 (d, J268.0, C-F Ar), 121.68 (d,J8.0, C Ar), 136.14, 151.09 (-C=O), 154.59 (C Ar), 156.50(C Ar), 158.87 (C Ar). LC-MS, m/z, (rel, %): 330.09 [M+H]+ (100). HRMS (FAB) Calc.: C13H11F4N5O:329.08997; Found: 330.0967 [M+H+].

Statistics shows that 3-(Trifluoromethyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine hydrochloride is playing an increasingly important role. we look forward to future research findings about 762240-92-6.

Reference:
Article; Mannam, Madhava Rao; Devineni, Subba Rao; Pavuluri, Chandra Mouli; Chamarthi, Naga Raju; Kottapalli, Raja Sekhara P.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 194; 9; (2019); p. 922 – 932;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem